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TCS Events

Show Up. Level Up. Connect.

Every TCS event is built around one goal leaving better than you arrived. Whether it’s a retreat with world-class speakers or an in-person mastermind, these events change businesses.
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Vector (27)

Annual Retreat

All-inclusive · 3 days · World-class speakers

Vector (28)

Semi-Annual Meetups

East & West Coast · In-person mastermind

Vector (29)

Weekly Zoom Calls

Live Executive Advisor · Expert-led · Members only

Past Retreat Speakers

  • Dr. Jordan B. Peterson
  • Ed Mylett
  • John Maxwell
  • Jesse Itzler

Upcoming Events

Mark Your Calendar

Meet-Up

November

2026

  • Pittsburgh

TCS Meet-UP Pittsburgh

Date: November 4–6, 2026

Location: The Distillery Complex (59 S 2nd St, Pittsburgh, PA 15219)

  • Connect with high-level contractors and business leaders during a three-day Pittsburgh meet-up built around growth, leadership, and real operator conversations.
  • Show up, level up, and build stronger systems through the TCS Meet-Up experience in partnership with Cool Hollow Mastermind: Pittsburgh Edition.
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Annual Retreat

FALL

2026
  • West Coast

West Coast In-Person Meetup

Same energy, different coast. Connect with members in the western region and walk away with new relationships, new ideas, and a renewed drive to execute.
  • Peer mastermind sessions real problems, real solutions
  • Open to all Inner Circle members and their affiliate member
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Always On

Virtual Executive Advisor Calls

Weekly

Inner Circle Executive Advisor Call
Live, trainer-led Zoom sessions covering sales, operations, hiring, finance, and more.

Inner Circle Members

2x / Mo

TCS Elite Executive Advisor Call

Twice-monthly group Executive Advisor sessions with industry experts. Come with questions, leave with answers.

Elite Members

Quarterly

1-on-1 Executive Session

A private 30-minute session with one of the TCS executive Executive Advisors focused entirely on your business.

All Members

Unlimited

1-on-1 Executive Session

Inner Circle members can book unlimited sessions with any of the 10 executive Executive Advisors. No caps.

Inner Circle Only

Don't Miss the Next Event.

Membership gets you access to every retreat, meetup, and Executive Advisor call on the calendar.

Apply for Membership